Methanol → Methyl 4-aminopyridine-2-carboxylate

HRID 1907878Notes

Reaction equation

HRID 1907878 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[CH:3]=1.S(=O)(=O)(O)O.[CH3:16]O>>[CH3:16][O:9][C:8](=[O:10])[C:4]1[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 20501324-Aminopicolinic acid

Product 1

HCID 3759117Methyl 4-aminopyridine-2-carboxylate

Procedure

A mixture of 4-aminopicolinic acid (2.50 g, 18.1 mmol) and conc. sulfuric acid (2 mL, 37.3 mmol) in 50 mL methanol was refluxed for 20 h. The mixture was concentrated i. vac., then 50 mL dichloromethane were added and made basic by addition of conc. ammonia (aq). Then water and NaCl (aq, sat.) were added and the aqueous layer was extracted with methylenechloride/methanol=9:1. The combined organic layers were dried over MgSO4 and then evaporated to dryness.

Workup

  1. temperaturewas refluxed for 20 h
  2. concentrationThe mixture was concentrated i
  3. addition, then 50 mL dichloromethane were added
  4. additionmade basic by addition of conc. ammonia (aq)
  5. additionThen water and NaCl (aq, sat.) were added
  6. extractionthe aqueous layer was extracted with methylenechloride/methanol=9:1
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-d9004f03d28548b49bba76d2a3c2b15e
Source dataset
uspto-grants-2013_12
Patent number
US08598190B2

Reaction notes

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